Abstract
A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.
| Original language | English |
|---|---|
| Pages (from-to) | 2462-2466 |
| Number of pages | 5 |
| Journal | Journal of Organic Chemistry |
| Volume | 80 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2015 Feb 20 |
Fingerprint
All Science Journal Classification (ASJC) codes
- Organic Chemistry
Cite this
}
Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins. / Lin, Mei Huey; Li, Yi Syuan; Kuo, Chung Kai; Chen, Chung Hao; Huang, Yen Chih; Liang, Kung Yu; Chen, Yu Chun; Tsai, Chang Hsien; Chuang, Tsung Hsun.
In: Journal of Organic Chemistry, Vol. 80, No. 4, 20.02.2015, p. 2462-2466.Research output: Contribution to journal › Article
TY - JOUR
T1 - Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins
AU - Lin, Mei Huey
AU - Li, Yi Syuan
AU - Kuo, Chung Kai
AU - Chen, Chung Hao
AU - Huang, Yen Chih
AU - Liang, Kung Yu
AU - Chen, Yu Chun
AU - Tsai, Chang Hsien
AU - Chuang, Tsung Hsun
PY - 2015/2/20
Y1 - 2015/2/20
N2 - A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.
AB - A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.
UR - http://www.scopus.com/inward/record.url?scp=84923339516&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84923339516&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b00072
DO - 10.1021/acs.joc.5b00072
M3 - Article
AN - SCOPUS:84923339516
VL - 80
SP - 2462
EP - 2466
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 4
ER -